His reasoning is that online stuff isn't bad even if it's coercive and manipulative.

You know it's going to be a shitfest when he writes:

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while her age was at first ambiguous – her photos revealed multiple piercings and tattoos, and a recent graduation could just as plausibly been undergrad. But prom was the tip-off. This piqued my interest.

He grooms her by pretending to be interested in her as a person for while but then:

as our communication transitioned from Facebook to iMessage, so did subtext become text – I started bugging Brandy for naked pictures. It's funny how that happens.

She tells him she doesn't want to send him naked pictures so this is what he does next:

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I would ask Brandy about her blowjob skills or share explicit details from my own sex life, but in the end I'd typically turn things back to a request for pictures.

Why does he keep pressuring her for pictures? Here's why:

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Whether it's flattery over your persistence or attrition or simply that if you keep asking, then eventually you'll catch her when she's bored enough to say yes,

But don't worry, it's not like he needs to see her nude:

Nudity was not even the objective necessarily; I was just as happy with panty shots – if only for the lewd frisson from writing the word "panties" to a girl.

His totally non creepy scheme eventually works.

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At first her position was unwavering. But after a few cycles of me perving past the boundaries of her comfort zone, then sitting back and waiting for her to get sufficiently annoyed at her ordinary life to start messaging me again, she caved, and caved magnificently.

Why does he think this is OK?

I provide her the opportunity to express her sexuality with an older, higher status male with no actual stakes.